ethyl (R)-4-((2R,6S)-6-((S)-4-(benzyloxy)-2-((tert-butyldiphenylsilyl)oxy)butyl)tetrahydro-2H-pyran-2-yl)-3-((triethylsilyl)oxy)butanoate | 1028456-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (R)-4-((2R,6S)-6-((S)-4-(benzyloxy)-2-((tert-butyldiphenylsilyl)oxy)butyl)tetrahydro-2H-pyran-2-yl)-3-((triethylsilyl)oxy)butanoate
• CAS: 1028456-16-7
• 化学式: C₄₄H₆₆O₆Si₂
• 分子量: 747.175
• InChiKey: GDJLIQWVIUBMDS-QYPPMKSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  52.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl (R)-4-((2R,6S)-6-((S)-4-(benzyloxy)-2-((tert-butyldiphenylsilyl)oxy)butyl)tetrahydro-2H-pyran-2-yl)-3-((triethylsilyl)oxy)butanoate 、 (三甲基硅基)甲基氯化镁 在 cerium(III) chloride 、 silica gel 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 45.5h， 以69%的产率得到tert-butyl-diphenyl-[(2S)-4-phenylmethoxy-1-[(2S,6R)-6-[(2S)-2-triethylsilyloxy-4-(trimethylsilylmethyl)pent-4-enyl]oxan-2-yl]butan-2-yl]oxysilane
  参考文献：
  名称：

  Efficient Synthetic Access to a New Family of Highly Potent Bryostatin Analogues via a Prins-Driven Macrocyclization Strategy

  摘要：

  The step-economical synthesis of a new class of bryostatin analogues that contain the complete oxycarbocyclic core ring system of the bryostatin natural products is reported. These agents are convergently assembled via a highly efficient, functional-group-tolerant, and stereoselective Prins-driven macrocyclization. These tetrahydropyranyl B-ring analogues are among our most potent and efficacious analogues to date, exhibiting nanomolar and picomolar activities in protein kinase C affinity assays as well as in cellular antiproliferation assays.

  DOI：

  10.1021/ja8015632
• 作为产物：
  描述：

  三乙基氯硅烷 、 4-{6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-yl}-3-hydroxybutyric acid ethyl ester 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以97%的产率得到ethyl (R)-4-((2R,6S)-6-((S)-4-(benzyloxy)-2-((tert-butyldiphenylsilyl)oxy)butyl)tetrahydro-2H-pyran-2-yl)-3-((triethylsilyl)oxy)butanoate
  参考文献：
  名称：

  Efficient Synthetic Access to a New Family of Highly Potent Bryostatin Analogues via a Prins-Driven Macrocyclization Strategy

  摘要：

  The step-economical synthesis of a new class of bryostatin analogues that contain the complete oxycarbocyclic core ring system of the bryostatin natural products is reported. These agents are convergently assembled via a highly efficient, functional-group-tolerant, and stereoselective Prins-driven macrocyclization. These tetrahydropyranyl B-ring analogues are among our most potent and efficacious analogues to date, exhibiting nanomolar and picomolar activities in protein kinase C affinity assays as well as in cellular antiproliferation assays.

  DOI：

  10.1021/ja8015632